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Related Concept Videos

Gene Regulation in Microbial Communities: Quorum Sensing01:28

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Quorum sensing is a mechanism of bacterial communication that enables coordinated gene expression in response to changes in population density. This facilitates collective behaviors that enhance survival, resource acquisition, and ecological adaptation. This process relies on small signaling molecules called autoinducers that accumulate as bacterial populations grow. When a critical threshold concentration of autoinducers is reached, bacterial cells collectively modify gene expression,...
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Bacterial signaling can occur within bacteria (intracellular) or between bacteria (intercellular). At times, a group of bacteria behaves like a community. To achieve this, they engage in quorum sensing, the perception of higher cell density that causes changes in gene expression. Quorum sensing involves both extracellular and intracellular signaling. The signaling cascade starts with a molecule called an autoinducer (AI). Individual bacteria produce AIs that move out of the bacterial cell...
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An Efficient Synthesis of Optically Active [4-13C] Labelled Quorum Sensing Signal Autoinducer-2.

Osvaldo S Ascenso1, Gonzalo Carrau1,2, Karina B Xavier3

  • 1Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, 2780-157 Oeiras, Portugal.

Molecules (Basel, Switzerland)
|January 15, 2021
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Summary

Researchers developed a novel synthetic method for Autoinducer-2 (AI-2), a key bacterial communication molecule. This new route enables the selective production of both enantiomers of AI-2 and its precursor, 4,5-dihydroxypentane-2,3-dione (DPD), including isotopically labeled versions.

Keywords:
13C-DPDAI-2DPDenantioselective synthesisquorum sensing

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Area of Science:

  • Organic Chemistry
  • Microbiology
  • Biochemistry

Background:

  • Quorum sensing (QS) is a cell-to-cell communication mechanism in bacteria.
  • Autoinducer-2 (AI-2) is a conserved signaling molecule involved in interspecies QS.
  • Efficient synthesis of AI-2 and its analogs is crucial for studying QS mechanisms.

Purpose of the Study:

  • To develop a new synthetic route for Autoinducer-2 (AI-2).
  • To prepare isotopically labeled [4-13C]-AI-2 and [1-13C]-AI-2.
  • To selectively synthesize both (R) and (S) enantiomers of the AI-2 precursor, 4,5-dihydroxypentane-2,3-dione (DPD).

Main Methods:

  • Enantioselective reduction of a ketone intermediate.
  • Synthesis of [4-13C]-AI-2 from [1-13C]-bromoacetic acid.
  • Preparation of both (R)- and (S)-DPD.

Main Results:

  • A novel synthetic pathway for AI-2 was established.
  • The method allows for the selective synthesis of both enantiomers of DPD.
  • Isotopically labeled [4-13C]-AI-2 and [1-13C]-AI-2 were successfully prepared.

Conclusions:

  • The developed synthetic route provides a versatile method for accessing AI-2 and its enantiomers.
  • This synthesis is valuable for producing labeled AI-2 for mechanistic studies.
  • The enantioselective reduction is a key step for controlling stereochemistry in AI-2 synthesis.